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Diastereoselective Alkylation of Activated Nitrogen Heterocycles with Alkenyl Boronate Complexes
James E McGettigan1, Joseph M Ready1
1Department of Biochemistry, Division of Chemistry, UT Southwestern Medical Center, 5323 Harry Hines Blvd., Dallas, TX 75390-0938, USA.
Abstract:
Alkenyl boronate complexes react with acylated quinolines and isoquinolines via 1,2-metalate rearrangement to give alkylated, dearomatized heterocycles in good yields, diastereoselectivities, and regioselectivities. This multi-component coupling is highly modular and can be used to access a wide scope of heterocyclic scaffolds. Chiral boronic esters made through this methodology possess high synthetic potential and can be transformed into various functional groups in one step without racemization.
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